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Synthese von 4‐Aminocinnolinen aus (Arylhydrazono)(cyan)‐essigsäurederivaten
Author(s) -
Gewald Karl,
Calderon Osmar,
Schäfer Harry,
Hain Ute
Publication year - 1984
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198419840715
Subject(s) - chemistry , thioamide , yield (engineering) , acetic acid , toluene , intramolecular force , medicinal chemistry , cyan , organic chemistry , art , materials science , metallurgy , visual arts
Synthesis of 4‐Aminocinnolines from (Arylhydrazono)(cyano)acetic Acid Derivatives The intramolecular Friedel‐Crafts reaction of (arylhydrazono)(cyano)acetamides and ‐malono‐nitriles 1 yields the 4‐amino‐3‐cinnolinecarboxylic acid derivatives 2 . Toluene as solvent takes part in the reaction of 1d and e and forms the 4‐amino‐3‐cinnolyl p ‐tolyl ketones 3 . Ethyl (phenylhydrazono)(cyano)acetate reacts in the presence of AlCl 3 to yield the 4‐hydroxy‐3‐cinnolinecarbonitrile ( 4 ). The pyrimido[5,4‐ c ]cinnolinone 6 , the 4‐amino‐3‐cinnolinecarboxylic acid 2g , and its thioamide 2h can be obtained from 2 .